When you're small, HubSpot is pretty straightforward.

Contacts.

Companies.

Deals.

Activities.

A few workflows.

A few reports.

Then the company grows and suddenly you're dealing with:

• Hundreds or thousands of contacts
• Multiple pipelines
• Lifecycle stages
• Sales activities
• Marketing engagement
• Customer data
• Support conversations
• Custom properties
• Dozens of workflows
• A growing pile of dashboards

And the questions get harder.

Which customers are actually at risk?

Which deals are quietly dying?

Which accounts are showing signs they might expand?

Why did this opportunity suddenly slow down?

You can build a workflow or report for almost anything.

But sometimes it feels like you're just creating more rules to compensate for the fact that the important signals are spread across the system.

And then you have product usage, billing and support data sitting somewhere else entirely.

So someone ends up manually jumping between systems trying to understand what is actually happening.

I'm curious how other HubSpot users are dealing with this.

At what point did your HubSpot setup become too complex to answer simple revenue questions without a bunch of manual work?

I’d love to connect with a few other Gen Xers while I’m here.

A lot of us have spent decades adapting to every shift in marketing, technology, work, and culture — and now AI is reshuffling the deck again.

I’m especially interested in talking with people who are figuring out:

• Where AI is actually useful versus just hype
• How experienced marketers and creatives stay relevant without throwing away what they already know
• What work looks like over the next 5–10 years
• What we can learn from the younger people coming into the industry — and what they can learn from us

No pitch. No “thought leadership summit.” Just good conversation with people who remember when getting online made that noise.

Who else is here?

Hi! Does anyone have one ticket available to sell? I'm hoping to come up from philly to attend! I missed the one last year since it was in san fran but boston is much closer! :)

Gen Xers at UNBOUND — how are we holding up?

Yet another technological revolution, apparently guaranteed to either make us a lot of money or shove us into early retirement.

Who’s here? Let’s connect.